33322-64-4

Upstream product

• 455-38-9 3-fluorobenzoic acid 
• 78162-58-0 N,N-dimethyl-1H-imidazole-1-sulfonamide 
• 13360-57-1 dimethylamino sulfonyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 137-26-8 Thiram 
• 1073-06-9 3-fluorobromobenzene 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 

Downstream Products

• 96660-77-4 N-<(3-Fluorphenyl)methoxymethylen>-N-methylmethanaminium-hexafluorophosphat 
• 96327-33-2 5-(3-Fluoro-benzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid 

Relevant academic research and scientific papers

Copper-catalyzed amidation of benzoic acids using tetraalkylthiuram disulfides as amine sources

A facile method for the copper-catalyzed synthesis of N-substituted benzamides was explored. In the presence of CuBr and di-tert-butyl peroxide, various N-substituted benzamides were prepared through amidation of benzoic acid by using commercially available and cheap tetraalkylthiuram disulfides as amine sources. With this protocol, a series of 14 N-substituted benzamides were furnished in good to excellent yields. The broad substrate scope and good to excellent yield show its practical synthetic value in organic synthesis.

Copper-catalyzed amide bond formation from formamides and carboxylic acids

A highly efficient copper-catalyzed approach to form amide bonds from formamides and carboxylic acids was developed. This protocol shows broad substrate scopes and high yields in the presence of 1 mol% catalyst and 4.0 equiv. formamides.

A novel method for the one-pot conversion of carboxylic acids to N,N-dimethylamides

A simple, efficient, and new method has been developed for the preparation of N,N-dimethylamides from carboxylic acids. As described below, treatment of a variety of aromatic carboxylic acids with N,N-dimethylsulfamoyl imidazole or N,N-dimethylsulfamoyl chloride in the presence of a mixture of methanesulfonic acid/phosphorus pentoxide (2:1, v/w) proceeded effectively to afford the corresponding N,N-dimethylamides inmoderate to good yields. Thismethod is easy, rapid, and good yielding for the synthesis of N,N-dimethylamides from carboxylic acids. Iranian Chemical Society 2012.

Variable Electronic Properties of the CSNMe2 Group

The ?I value for the CSNMe2 group has been determined and the value of 0.23 indicates that this group is inductively electron withdrawing.The effect of the p-CSNMe2 group on the solvolysis rate of cumyl chloride has also been determined and, relative to the p-H analogue, this group has a negligible effect on rate. p-CSNMe2 substitution slows the hydrolysis rate of substituted benzaldehyde dimethyl acetals. p-CSNMe2 substitution enhances the solvolysis rate of ArCH(OMs)PO(OEt)2.These variable rate effects on reactions involving cationic intermediates have been interpreted in terms of variable electronic properties of the CSNMe2 group.This group can be cation stabilizing, electroneutral, or cation destabilizing, depending on the charge demands of specific cations.This is a result of a conjugative interaction of CSNMe2 with a cationic center and resultant delocalization of positive charge onto sulfur.The importance of such conjugation is a function of the amount of transition-state charge developed on the carbon bearing the CSNMe2 group.The electronic effects of the amphielectronic p-CSNMe2 group are compared to the more conventional effects of CONMe2 and the m-CSNMe2 analogues.